Dutasteride

Dutasteride
Clinical data
Pronunciation	/duˈtæstəˌraɪd/; doo-TA-stə-RYDE
Trade names	Avodart, others
Other names	GG-745; GI-198745; GI-198745X; N-[2,5-Bis(trifluoromethyl)phenyl]-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
AHFS/Drugs.com	Monograph
MedlinePlus	a603001
License data	US DailyMed: Dutasteride;
Pregnancy; category	Not to be used during pregnancy;
Routes of; administration	By mouth
Drug class	5α-Reductase inhibitor
ATC code	G04CB02 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	60%
Protein binding	99%
Metabolism	Liver (CYP3A4)
Metabolites	• 4'-Hydroxydutasteride; • 6'-Hydroxydutasteride; • 1,2-Dihydrodutasteride; (All three active)
Elimination half-life	4–5 weeks
Excretion	Feces: 40% (metabolites); Urine: 5% (unchanged)
Identifiers
	IUPAC name (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide;
CAS Number	164656-23-9 ;
PubChem CID	6918296;
IUPHAR/BPS	7457;
DrugBank	DB01126 ;
ChemSpider	5293502 ;
UNII	O0J6XJN02I;
KEGG	D03820 ;
ChEBI	CHEBI:521033 ;
ChEMBL	ChEMBL1200969 ;
CompTox Dashboard (EPA)	DTXSID8046452 ;
ECHA InfoCard	100.166.372
Chemical and physical data
Formula	C27H30F6N2O2
Molar mass	528.539 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.346 g/cm3 at 294 K (calculated)
	SMILES FC(F)(F)c1cc(c(cc1)C(F)(F)F)NC(=O)[C@@H]3[C@]2(CC[C@H]4[C@H]([C@@H]2CC3)CC[C@H]5NC(=O)\C=C/[C@]45C)C;
	InChI InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1 ; Key:JWJOTENAMICLJG-QWBYCMEYSA-N ;
	(verify)

Dutasteride, sold under the brand name Avodart among others, is a medication primarily used to treat the symptoms of a benign prostatic hyperplasia (BPH), an enlarged prostate not associated with cancer. It is also used to treat pattern hair loss in men as an off-label medication and as an approved medication in South Korea, Japan, and Taiwan. A few months may be required before benefits occur. Dutasteride may also be used as a part of hormone therapy in transgender women. It is usually taken by mouth; however, topical versions exist for those with hair loss, which are designed to minimize systemic exposure by acting specifically on hair follicles.

The most commonly reported side effects of dutasteride, although rare, include sexual dysfunction. In the largest available study of 6,729 men with BPH, 9% experienced erectile dysfunction (compared to 5.7% treated with a placebo), 3.3% experienced decreased sex drive (vs 1.6% of placebo), and 1.9% had enlarged breasts (vs 1% of placebo). Exposure during pregnancy is specifically contraindicated because antiandrogens such as dutasteride have been shown to interfere with the sexual development of male fetuses.

Dutasteride was patented in 1993 by Glaxo Wellcome (later known as GSK after additional mergers) and was approved for medical use in 2001. It is available as a generic medication and as such, manufactured and exported more by India than elsewhere. In 2023, it was the 236th most commonly prescribed medication in the US with more than 1 million prescriptions.